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Synlett 1994; 1994(11): 969-971
DOI: 10.1055/s-1994-23068
DOI: 10.1055/s-1994-23068
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Enantioselective Synthesis of Allylic Alcohols via Asymmetric [2,3]-Sigmatropic Meisenheimer Rearrangement
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Publication History
Publication Date:
22 March 2002 (online)
Various allylic alcohols 6 are prepared in high enantiomeric excesses (ee = 93 - 99 %) by oxidation of readily available allylamines 3 bearing a C2-symmetrical amine moiety, followed by a [2,3]-sigmatropic Meisenheimer rearrangement of the resulting amine-N-oxide 4 and reductive N,O-bond cleavage of hydroxylamines 5.